Triphenyltin hydride is the

organotin compound Organotin chemistry is the scientific study of the synthesis and properties of organotin compounds or stannanes, which are organometallic compounds containing tin–carbon bonds. The first organotin compound was diethyltin diiodide (), discovered ...

with the formula (C₆H₅)₃SnH. It is a colorless distillable oil that is soluble in organic solvents. It is often used as a source of "H·" to generate

radicals Radical (from Latin: ', root) may refer to: Politics and ideology Politics *Classical radicalism, the Radical Movement that began in late 18th century Britain and spread to continental Europe and Latin America in the 19th century *Radical politics ...

or cleave carbon-oxygen bonds.

Preparation and reactions

Ph₃SnH, as it is more commonly abbreviated, is prepared by treatment of

triphenyltin chloride Triphenyltin chloride is an organotin compound with formula Sn(C6H5)3Cl. It is a colourless solid that dissolves in organic solvents and slowly reacts with water. Applications The main use for this compound is as a fungicide and antifoulant. Tr ...

with

lithium aluminium hydride Lithium aluminium hydride, commonly abbreviated to LAH, is an inorganic compound with the chemical formula or . It is a white solid, discovered by Finholt, Bond and Schlesinger in 1947. This compound is used as a reducing agent in organic synthe ...

.Clive, D. L. J. "Triphenylstannane" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. Although Ph₃SnH is treated as a source of "H·", in fact it does not release free

hydrogen atom A hydrogen atom is an atom of the chemical element hydrogen. The electrically neutral hydrogen atom contains a single positively charged proton in the nucleus, and a single negatively charged electron bound to the nucleus by the Coulomb for ...

s, which are extremely reactive species. Instead, Ph₃SnH transfers H to substrates usually via a radical chain mechanism. This reactivity exploits the relatively good stability of "Ph₃Sn·"

References

{{reflist Metal hydrides Triphenyltin compounds Reagents for organic chemistry